TWI597261B - 含ｃｆｏ之烯胺酮類及其用於製備含ｃｆｏ之吡唑類的用途 - Google Patents
含ｃｆｏ之烯胺酮類及其用於製備含ｃｆｏ之吡唑類的用途 Download PDFInfo
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- TWI597261B TWI597261B TW102104714A TW102104714A TWI597261B TW I597261 B TWI597261 B TW I597261B TW 102104714 A TW102104714 A TW 102104714A TW 102104714 A TW102104714 A TW 102104714A TW I597261 B TWI597261 B TW I597261B
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- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- UHNSRFWQBVXBSK-UHFFFAOYSA-N methanol;2,2,2-trifluoroacetic acid Chemical class OC.OC(=O)C(F)(F)F UHNSRFWQBVXBSK-UHFFFAOYSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
- GVZFDPPAJXHNGL-UHFFFAOYSA-N trifluoromethyl trifluoromethanesulfonate Chemical compound FC(F)(F)OS(=O)(=O)C(F)(F)F GVZFDPPAJXHNGL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12356003.9A EP2628722A1 (en) | 2012-02-16 | 2012-02-16 | CF3O-containing enaminoketones and their utilization for the preparation of CF3O-containing pyrazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201336810A TW201336810A (zh) | 2013-09-16 |
| TWI597261B true TWI597261B (zh) | 2017-09-01 |
Family
ID=47716032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102104714A TWI597261B (zh) | 2012-02-16 | 2013-02-07 | 含ｃｆｏ之烯胺酮類及其用於製備含ｃｆｏ之吡唑類的用途 |
Country Status (12)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102410034B1 (ko) | 2014-03-24 | 2022-06-15 | 바이엘 크롭사이언스 악티엔게젤샤프트 | α,α-디할로아민 및 케트이민으로부터 3,5-비스(할로알킬)피라졸 유도체의 제조방법 |
| EP3015458A1 (en) * | 2014-11-03 | 2016-05-04 | Bayer CropScience AG | Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines |
| US10273215B2 (en) | 2015-06-26 | 2019-04-30 | Bayer Cropscience Aktiengesellschaft | Process for preparing substituted pyrazoles containing haloalkoxy- and haloalkylthio groups from alpha,alpha -dihaloalkylamines and ketimines |
| CN115322152A (zh) * | 2016-10-19 | 2022-11-11 | Ａｇｃ株式会社 | 含氮化合物的制造方法 |
| UA127065C2 (uk) | 2018-04-25 | 2023-03-29 | Баєр Акціенгезельшафт | Нові гетероарил-триазольні та гетероарил-тетразольні сполуки як пестициди |
| EP4495125A1 (en) * | 2023-07-19 | 2025-01-22 | Freie Universität Berlin | A catalyst free synthesis method for introducing a trifluoromethoxy moiety into at least one organic compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1071162A (zh) * | 1991-10-09 | 1993-04-21 | 罗纳-普朗克农业化学公司 | 新型苯基吡唑杀真菌剂 |
| WO1994029300A1 (fr) * | 1993-06-07 | 1994-12-22 | Rhone Poulenc Agrochimie | Fongicides pyrazoles substitues en position 3 par un heterocycle |
| WO2006032851A1 (en) * | 2004-09-20 | 2006-03-30 | Biolipox Ab | Pyrazole compounds useful in the treatment of inflammation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2743473B2 (ja) * | 1988-07-04 | 1998-04-22 | 日産化学工業株式会社 | ピラゾールカルボン酸類の製造方法 |
| JPH09169736A (ja) * | 1995-12-21 | 1997-06-30 | Nissan Chem Ind Ltd | ピラゾール誘導体及び有害生物防除剤 |
| DE102006050516A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| WO2009001126A1 (en) | 2007-06-27 | 2008-12-31 | Astrazeneca Ab | Substituted piperidine derivatives and their use as antibaterial agents |
| DE102007036702A1 (de) * | 2007-08-03 | 2009-02-05 | Bayer Cropscience Ag | Synergistische kulturpflanzenverträgliche herbizide Kombinationen enthaltend Herbizide aus der Gruppe der Pyrazolyloxyphenyl-Derivate |
| WO2009140342A1 (en) * | 2008-05-16 | 2009-11-19 | Schering Corporation | Glucagon receptor antagonists, compositions, and methods for their use |
| DE102008024221A1 (de) | 2008-05-19 | 2009-11-26 | Merck Patent Gmbh | Herstellung von CF3O-Gruppen enthaltenden Verbindungen |
-
2012
- 2012-02-16 EP EP12356003.9A patent/EP2628722A1/en not_active Withdrawn
-
2013
- 2013-02-07 TW TW102104714A patent/TWI597261B/zh not_active IP Right Cessation
- 2013-02-13 MX MX2014009442A patent/MX368424B/es active IP Right Grant
- 2013-02-13 US US14/378,372 patent/US9096535B2/en not_active Expired - Fee Related
- 2013-02-13 ES ES13704421T patent/ES2701082T3/es active Active
- 2013-02-13 KR KR1020147024063A patent/KR102085012B1/ko not_active Expired - Fee Related
- 2013-02-13 EP EP13704421.0A patent/EP2822925B1/en not_active Not-in-force
- 2013-02-13 BR BR112014019346-0A patent/BR112014019346B1/pt not_active IP Right Cessation
- 2013-02-13 CN CN201380009409.3A patent/CN104220419B/zh not_active Expired - Fee Related
- 2013-02-13 DK DK13704421.0T patent/DK2822925T3/en active
- 2013-02-13 JP JP2014557016A patent/JP6212056B2/ja not_active Expired - Fee Related
- 2013-02-13 WO PCT/EP2013/052829 patent/WO2013120876A1/en active Application Filing
-
2014
- 2014-07-13 IL IL233625A patent/IL233625A/en active IP Right Grant
-
2017
- 2017-05-30 JP JP2017106304A patent/JP2018008928A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1071162A (zh) * | 1991-10-09 | 1993-04-21 | 罗纳-普朗克农业化学公司 | 新型苯基吡唑杀真菌剂 |
| WO1994029300A1 (fr) * | 1993-06-07 | 1994-12-22 | Rhone Poulenc Agrochimie | Fongicides pyrazoles substitues en position 3 par un heterocycle |
| WO2006032851A1 (en) * | 2004-09-20 | 2006-03-30 | Biolipox Ab | Pyrazole compounds useful in the treatment of inflammation |
Non-Patent Citations (1)
| Title |
|---|
| 李明, "烯胺酮的合成及其在有機合成中的應用", Chinese Journal of Organic Chemistry, 2006, 26, 1192-1207 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2018008928A (ja) | 2018-01-18 |
| DK2822925T3 (en) | 2019-01-07 |
| JP6212056B2 (ja) | 2017-10-11 |
| JP2015511944A (ja) | 2015-04-23 |
| IL233625A0 (en) | 2014-08-31 |
| CN104220419A (zh) | 2014-12-17 |
| TW201336810A (zh) | 2013-09-16 |
| MX2014009442A (es) | 2014-11-12 |
| KR102085012B1 (ko) | 2020-03-05 |
| CN104220419B (zh) | 2017-03-29 |
| MX368424B (es) | 2019-10-02 |
| EP2822925B1 (en) | 2018-09-05 |
| US20150018561A1 (en) | 2015-01-15 |
| EP2628722A1 (en) | 2013-08-21 |
| BR112014019346B1 (pt) | 2020-09-15 |
| KR20150002596A (ko) | 2015-01-07 |
| ES2701082T3 (es) | 2019-02-20 |
| BR112014019346A2 (enrdf_load_stackoverflow) | 2017-06-20 |
| WO2013120876A1 (en) | 2013-08-22 |
| IL233625A (en) | 2017-10-31 |
| EP2822925A1 (en) | 2015-01-14 |
| US9096535B2 (en) | 2015-08-04 |
| BR112014019346A8 (pt) | 2017-07-11 |
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